Lately I've only been offered the executive room at extra cost, when I would expect to have an upgrade anyway (LTP).
Are you booking at the very earliest the inventory is made available? It's not surprising that the "base" award rooms go first, leaving extra cost/upgraded rooms available. Check the property you are looking at for 350 days out, Saturday evening when they're made available and see what's there.
Any specific property?
The fact that you "expect" an upgrade has nothing to do with it.